Fluoride Ion → HCID 178465491, compound

HRID 585717Notes

Reaction equation

HRID 585717 reaction equation
[CH2:1]([NH:3][C:4](=[O:34])[O:5][C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][Si](C(C)(C)C)(C)C)=[CH:14][C:13]=2[O:26][Si](C(C)(C)C)(C)C)[CH2:8][CH2:7]1)[CH3:2].[F-]>CO>[CH2:1]([NH:3][C:4](=[O:34])[O:5][C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][C:13]=2[OH:26])[CH2:8][CH2:7]1)[CH3:2]

Participants

4

Reactant 2

HCID 28179Fluoride IonHCID 178465492HCID 178465492, compound

Product 1

HCID 178465491HCID 178465491, compoundYield 242.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of trans-4-(2,4-bis{[tert-butyl(dimethyl)silyl]oxy}phenyl)cyclohexyl ethylcarbamate (18 mg), methanol (10 ml) and Amberlyst fluoride resin (0.3 g) were stirred at room temperature for 24 hr. The reaction mixture was filtered, and the filtrate was evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, ethyl acetate/petrol, 1:3 v/v) to give the title compound as a white solid (24 mg, 87%). δH (CD3OD) 1.10 (3H, t), 1.40-1:60 (4H, m), 1.80-1.90 (2H, m), 2.00-2.10 (2H, m), 2.72-2.80 (1H, m), 3.10 (2H, t), 4.50-4.60 (1H, m), 6.20-6.26 (2H, m), 6.88 (1H, d); m/z (ES+) 280 (M+H)+.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was evaporated in vacuo
  3. customThe residue was purified by flash column chromatography (SiO2, ethyl acetate/petrol, 1:3 v/v)

Sources & evidence

ORD record
ord-74394af517e04e5185c967b948cf69e1
Source dataset
uspto-grants-2005_08
Patent number
US06933319B2

Reaction notes

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